Dukes County MA Homes for Sale

/28
$1,095,000

$100K PRICE DROP
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
2 Winemack St, Oak Bluffs, MA 02557

Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping,

Rene Ben David

Ocean Park Realty Inc

2 Winemack St, Oak Bluffs, MA 02557
/43
$12,250,000
- 7 Beds
- 4 Baths
- 4,855 Sq Ft
139 Chappaquiddick Rd, Edgartown, MA 02539

You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of

Katherine Donahue Sandpiper Realty

139 Chappaquiddick Rd, Edgartown, MA 02539
/40
$1,695,000

$100K PRICE DROP
- 3 Beds
- 3 Baths
- 3,702 Sq Ft
174 Middle Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

Sheila Morse Island Real Estate

174 Middle Rd, Chilmark, MA 02535
/46
$2,490,000
- 3 Beds
- 3.5 Baths
- 3,579 Sq Ft
8 Jeffers Way, Aquinnah, MA 02535

Tucked away on more than two acres along a private dirt road, this extensively updated post-and-beam home offers exceptional space and privacy in a peaceful Aquinnah setting. The property is surrounded by woodlands, open fields, streams, and ancient stone walls and is located approximately one mile from Aquinnah’s resident beaches.With over 3,500 square feet, this home offers generous

Jennifer O'hanlon Compass LLC

8 Jeffers Way, Aquinnah, MA 02535
/20
$1,525,000

$75K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,334 Sq Ft
150 Field View Ln, Vineyard Haven, MA 02568

A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

Sheila Morse Island Real Estate

150 Field View Ln, Vineyard Haven, MA 02568
/3
$450,000
- Land
- 6,503 Sq Ft
- $3,014,066 per Acre
00 Moshup Trail Unit 14.2, Aquinnah, MA 02535

Become one of only 21 members to access the exclusive Goff Beach, a gated community with parking. Traverse to the top of the sandy dune and overlook the sparkling ocean with wide sandy beach. A special opportunity rarely offered for sale. 0.15-acre parcel offers direct access to one of the most desirable stretches of shoreline on Martha’s Vineyard. Situated to the right of the Rainbow House, the

Rebecca V Conroy Conroy & Company R.E., Inc.

00 Moshup Trail Unit 14.2, Aquinnah, MA 02535
/45
$1,595,000

Open Sat 12PM - 2PM $30K PRICE DROP
- 4 Beds
- 3 Baths
- 1,898 Sq Ft
20 Hidden Cove Rd, Oak Bluffs, MA 02557

Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded

Jennifer DaSilva Compass | Point B

20 Hidden Cove Rd, Oak Bluffs, MA 02557
/49
$9,750,000
- 7 Beds
- 5 Baths
- 3,617 Sq Ft
23 Flanders Ln, Chilmark, MA 02535

A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

Julianna Flanders Flanders Real Estate

23 Flanders Ln, Chilmark, MA 02535
/56
$16,250,000
- 6 Beds
- 8 Baths
- 8,648 Sq Ft
25 Brickyard Rd, Chilmark, MA 02535

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

Peyton Wallace Studio Realty LLC

25 Brickyard Rd, Chilmark, MA 02535
/46
$3,900,000
- 3 Beds
- 4 Baths
- 2,960 Sq Ft
3 Bens Way, Chilmark, MA 02535

Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and

Russell Maloney Russell Maloney Real Estate

3 Bens Way, Chilmark, MA 02535
/2
$399,000

$26K PRICE DROP
- Land
- 7,840 Sq Ft
- $2,216,667 per Acre
0 Heather Ln Unit 56, Oak Bluffs, MA 02568

Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

Jennifer DaSilva Compass | Point B

0 Heather Ln Unit 56, Oak Bluffs, MA 02568
/18
$2,500,000
- 3 Beds
- 3.5 Baths
- 1,884 Sq Ft
77 Sixth St N, Edgartown, MA 02539

WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living

Michele Casavant Vineyard Village Realty

77 Sixth St N, Edgartown, MA 02539
/46
$2,695,000

$255K PRICE DROP
- 5 Beds
- 4 Baths
- 2,374 Sq Ft
124 Main St, Vineyard Haven, MA 02568

Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

124 Main St, Vineyard Haven, MA 02568
/2
$399,000

$26K PRICE DROP
- Land
- 7,840 Sq Ft
- $2,216,667 per Acre
0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568

Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

Jennifer B. DaSilva Compass

0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
/46
$15,250,000
- 7 Beds
- 7 Baths
- 6,726 Sq Ft
14 Starbuck Neck Rd, Edgartown, MA 02539

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the

Mark Jenkins Wallace & Co. Sotheby's

14 Starbuck Neck Rd, Edgartown, MA 02539
/16
$1,500,000
- 3 Beds
- 2 Baths
- 1,717 Sq Ft
8 Pipn Cir, Edgartown, MA 02539

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

8 Pipn Cir, Edgartown, MA 02539
/33
$1,095,000

$130K PRICE DROP
- 1 Bed
- 2 Baths
- 1,428 Sq Ft
323 County Rd, Oak Bluffs, MA 02557

This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment.The home features a bright, open-concept kitchen, dining,

Nancy Beckwith Anchor Realty of Martha's Vineyard

323 County Rd, Oak Bluffs, MA 02557
/26
$1,285,000

$35K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,347 Sq Ft
41 Cook Rd, Vineyard Haven, MA 02568

Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An

Jennifer O'hanlon Compass

41 Cook Rd, Vineyard Haven, MA 02568
/19
$1,195,000

$100K PRICE INCREASE
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
170 Barnes Rd, Oak Bluffs, MA 02557

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

Christine Rose Martha's Vineyard Island-Wide Realty

170 Barnes Rd, Oak Bluffs, MA 02557
/36
$3,975,000
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
99 Ocean Ave, Oak Bluffs, MA 02557

A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and

Perry Patterson MV Luxury Homes

99 Ocean Ave, Oak Bluffs, MA 02557
/18
$239,000
- 1 Bed
- 1 Bath
- 316 Sq Ft
33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

Rene Jackson Island Real Estate

33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
/6
$1,895,000
- Land
- 1.87 Acres
- $1,014,997 per Acre
22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless beauty of Martha’s Vineyard converge.This 1.87-acre homesite represents the final opportunity to

Marilyn Moses Ocean Park Realty Inc

22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
/54
$1,150,000
- 3 Beds
- 1.5 Baths
- 1,284 Sq Ft
41 Renear St, Vineyard Haven, MA 02568

Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together.Set on a generous .26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an

Leslie C. Floyd Portfolio Properties

41 Renear St, Vineyard Haven, MA 02568
/17
$899,000

$96K PRICE DROP
- 3 Beds
- 1 Bath
- 1,264 Sq Ft
36 Circuit Ave, Vineyard Haven, MA 02568

This cared for contemporary is located in a mature neighborhood abutting Sheriff's Meadow. It has a three bedroom, one bath reverse floor-plan design that captures ample natural light from a serene park-like setting. Hardwoods and ceramic tile flooring, A/C mini-split heat-pumps, a rear balcony deck, outdoor shower, and a delightful terraced patio compliment this new opportunity. *Seller is

Sean Federowicz Landmarks at TODAY Real Estate

36 Circuit Ave, Vineyard Haven, MA 02568
/42
$2,145,000

$105K PRICE DROP
- 4 Beds
- 3 Baths
- 1,918 Sq Ft
21 & 25 Fulling Mill Rd, Chilmark, MA 02535

Jessie Holtham Wallace & Co. Sotheby's International Realty

21 & 25 Fulling Mill Rd, Chilmark, MA 02535
/38
$3,200,000
- 4 Beds
- 6 Baths
- 3,428 Sq Ft
19 Llewellyn Way, Edgartown, MA 02539

Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

19 Llewellyn Way, Edgartown, MA 02539
/35
$6,650,000
- 6 Beds
- 6 Baths
- 4,664 Sq Ft
38 Simpsons Ln, Edgartown, MA 02539

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six

Thomas Leclair Landvest MV

38 Simpsons Ln, Edgartown, MA 02539
/25
$5,495,000

$500K PRICE DROP
- 3 Beds
- 3 Baths
- 2,234 Sq Ft
43 Sengekontacket Rd, Oak Bluffs, MA 02557

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

Peyton Wallace Studio Realty LLC

43 Sengekontacket Rd, Oak Bluffs, MA 02557
/39
$3,295,000
- 5 Beds
- 4 Baths
- 2,330 Sq Ft
29 and 33 Lagoon Pond Rd, Tisbury, MA 02568

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

Madelyn Silvia Wallace & Co. Sotheby's International Realty

29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
/43
$2,455,000

$20K PRICE DROP
- 4 Beds
- 4 Baths
- 3,039 Sq Ft
99 The Blvd, Edgartown, MA 02539

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury.The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private

Jennifer DaSilva Compass | Point B

99 The Blvd, Edgartown, MA 02539
/25
$6,500,000
- 6 Beds
- 7 Baths
- 4,753 Sq Ft
16 Red Coat Hill Rd, Vineyard Haven, MA 02568

Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

Joe & Nicole Holland Vineyard Dream Realty LLC

16 Red Coat Hill Rd, Vineyard Haven, MA 02568
/37
$389,900
- 1 Bed
- 1.5 Baths
- 584 Sq Ft
21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568

HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND!!! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE & PRICED APPROX $100,000 less than an identical unit that Just Sold this summer!!Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you’re not here, the management team will rent

Susan Austin Austin R.E. Properties of MV

21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
/20
$2,425,000
- 2 Beds
- 2 Baths
- 895 Sq Ft
131 N Water St Unit 62, Edgartown, MA 02539

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services.

Mitzi Lawlor Corcoran Property Advisors

131 N Water St Unit 62, Edgartown, MA 02539
/8
$2,725,000
- Land
- 7.6 Acres
- $358,553 per Acre
34 Ebens Ln, Chilmark, MA 02535

This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience --

Peyton Wallace Studio Realty LLC

34 Ebens Ln, Chilmark, MA 02535
/17
$2,595,000
- 2 Beds
- 2 Baths
- 960 Sq Ft
131 N Water St Unit 22, Edgartown, MA 02539

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services.

Mitzi Lawlor Corcoran Property Advisors

131 N Water St Unit 22, Edgartown, MA 02539
/17
$2,875,000
- 3 Beds
- 3 Baths
- 1,061 Sq Ft
131 N Water St Unit 96, Edgartown, MA 02539

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft., second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services.

Mitzi Lawlor Corcoran Property Advisors

131 N Water St Unit 96, Edgartown, MA 02539
/41
$2,595,000

$55K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,858 Sq Ft
59 Tuckernuck Ave, Oak Bluffs, MA 02557

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood

Jennifer B. DaSilva Compass

59 Tuckernuck Ave, Oak Bluffs, MA 02557
/5
$789,000
- Land
- 16,988 Sq Ft
- $2,023,077 per Acre
24 Towanticut St, Oak Bluffs, MA 02568

OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut

Alisan Lohan - Conway Alisan Lohan - Conway Properties

24 Towanticut St, Oak Bluffs, MA 02568
/57
$3,295,000
- 5 Beds
- 4 Baths
- 2,330 Sq Ft
29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive

Madelyn Silvia Wallace & Co. Sotheby's

29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
/41
$7,695,000

New Construction $255K PRICE DROP
- 4 Beds
- 4.5 Baths
- 7,766 Sq Ft
2 Lexington Ave, Edgartown, MA 02539

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors

Peyton Wallace Studio Realty LLC

2 Lexington Ave, Edgartown, MA 02539

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